ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate

Base Information

• Chemical Name: ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate
• CAS No.: 223526-69-0
• Molecular Formula: C₄₀H₅₄FN₃O₉
• Molecular Weight: 739.882
• Mol file: 223526-69-0.mol

Synonyms:ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate

Chemical Property of ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate

There total 9 articles about ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid (223526-67-8) + (E)-(S)-4-Amino-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-pyrrolidin-3-yl]-pent-2-enoic acid ethyl ester; hydrochloride → ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate (223526-69-0)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 23 ℃; Yield given;

DOI:10.1021/jm9805384

Reference yield:

(4S)-4-(2-methoxycarbonylethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (136904-77-3) → ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate (223526-69-0)

Guidance literature:

Multi-step reaction with 9 steps

1: aq. 4.0 M NaOH / methanol / 3.5 h / 23 °C

2: 1.) pivaloyl chloride, Et₃N, 2.) LiCl / 1.) THF, 0 deg C, 3.5 h, 2.) THF, 23 deg C, 19 h

3: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 3 h, b) -45 deg C, 2 h

4: 1.) O₃, CH₃OH, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, a) -78 deg C, 3.5 h, b) 0 deg C, 1 h

5: 1.) NaOAc, NaCNBH₃, 2.) TsOH*H₂O / 1.) THF, EtOH, 23 deg C, 20 h, 2.) CH₃OH, 50 deg C, 2.5 h

6: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -78 deg C, 1.5 h

7: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 45 min

8: 4.0 M HCl / dioxane / 1.5 h / 23 °C

9: 1-hydroxybenzotriazole hydrate, 4-methymorpholine, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 23 °C

With 4-methyl-morpholine; hydrogenchloride; methanol; sodium hydroxide; oxalyl dichloride; dimethylsulfide; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; sodium cyanoborohydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium chloride; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jm9805384

Reference yield:

(4S)-4-(2'-carboxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (223526-25-8) → ethyl-3--L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate (223526-69-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) pivaloyl chloride, Et₃N, 2.) LiCl / 1.) THF, 0 deg C, 3.5 h, 2.) THF, 23 deg C, 19 h

2: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 3 h, b) -45 deg C, 2 h

3: 1.) O₃, CH₃OH, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, a) -78 deg C, 3.5 h, b) 0 deg C, 1 h

4: 1.) NaOAc, NaCNBH₃, 2.) TsOH*H₂O / 1.) THF, EtOH, 23 deg C, 20 h, 2.) CH₃OH, 50 deg C, 2.5 h

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -78 deg C, 1.5 h

6: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 45 min

7: 4.0 M HCl / dioxane / 1.5 h / 23 °C

8: 1-hydroxybenzotriazole hydrate, 4-methymorpholine, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 23 °C

With 4-methyl-morpholine; hydrogenchloride; methanol; oxalyl dichloride; dimethylsulfide; sodium acetate; sodium hexamethyldisilazane; pivaloyl chloride; sodium cyanoborohydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium chloride; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm9805384

upstream raw materials:

(2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid

(4S)-4-(2-methoxycarbonylethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

(4S)-4-(2'-carboxyethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

{(S)-2-[(S)-1-(2,4-Dimethoxy-benzyl)-2-oxo-pyrrolidin-3-yl]-1-formyl-ethyl}-carbamic acid tert-butyl ester

Downstream raw materials:

ethyl-3-<(5'-methylisoxazole-3'-carbonyl)-L-ValΨ-L-Phe(4-F)-L-<(N-2,4-dimethoxybenzyl)-(S)-Pyrrol-Ala>>-E-propenoate